


Rider's New Ride

by HeroFizzer



Category: Fate/stay night & Related Fandoms
Genre: Bondage, F/M, Femdom, Pegging, Sensory Deprivation
Language: English
Status: Completed
Published: 2020-10-11
Updated: 2020-10-13
Packaged: 2021-03-07 21:20:35
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 6,936
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/26944327
Author URL: https://archiveofourown.org/users/HeroFizzer/pseuds/HeroFizzer
Summary: Tired of Rider taking his family's motorcycle out on repeat, Shirou banishes her to using the lesser of the two. Upset with the lack of joy in her joyriding, the Servant stumbles upon the best way to teach the young man who's really in charge of the rides by making him one of hers. (Commissioned)
Relationships: Emiya Shirou/Medusa | Rider
Comments: 1
Kudos: 18





	1. Chapter 1

“Rider! Medusa! Get in here now!”

Rider sighed, as it was never a good sign when Shirou Emiya called on her by both of her names. She remained stoic in her emotions, as it didn't seem too surprising that he was calling for her. There were a good number of reasons for that to happen, although she decided not to address that and see just what it was in particular he was calling on her for this time.

Stepping into the dining room, Rider took a moment to politely bow her head to Shirou, ignoring the glare in his eyes as he remained seated. “Yes, Shirou?” she asked.

“We need to talk about your driving habits,” Shirou said, “and the fact that you keep using the family motorcycle for all of your reckless driving.”

“It's not reckless,” Rider corrected him, “it's a serious need for me to go out and feel the breeze against my face.” Considering that more than half of her face was covered by a helmet and visor whenever she went riding, Shirou somehow had his doubts regarding that. “I see you're not taking me seriously, Shirou, so let me try to address this as best I can: I love the speeds that I can go at when riding that motorcycle. I can't get enough of the rush, or the feeling when I pull off some of the moves I can do when I go fast enough.”

Shirou nodded his head. “I can understand that, given that you’re a Rider class Servant. But you put the bike in such rough shape every time you're done with it, I have to take a moment to decide whether it’s worth repairing or scrapping for parts! Do you have any idea how much time and money I’ve had to spend repairing it in just the last month?! The brakes alone are a serious pain to remove and replace. And that's not even getting into the fact the tires are not only badly worn down whenever you come back from your joyrides, but they're also so hot I get worried they'll melt into the garage's pavement!”

“I'm sorry,” said Rider, “but there's nothing I can do about that, Shirou.”

“No, there certainly is,” Shirou sighed, “because from now on I'm forbidding you from using the motorcycle to do any more of your crazy driving!”

“Excuse me?” gasped Rider, quivering as if her heart had just been ripped out and crushed.

“Until you understand how much of a pain it is to clean up after your messes, you're only limited to using the safer of the two bikes.”

“But... that one is useless to me!” Rider argued. “It only ever gets used by the others for casual strolls and grocery pickups! It can never give me the kind of thrill I need!”

“And who do you think is to blame for that?” Shirou asked, his expression firm as he kept his eyes on Medusa’s distraught gaze. “You've been warned time and time again, Rider. It's time you finally understand the consequences of your actions.”

Rider could stand there all day and argue with the boy, but unfortunately, she knew there was very little she could do, as this was his house she lived under, and at the end of the day the Number 1 bike was in fact his property. Shirou was adamant in his decisions once he made them, and Rider knew that nothing she could say was going to change his mind on this one.

There was only one thing she could think to do, even if she knew full well that in this circumstance it would only serve to infuriate her. “I need to go for a ride,” she growled, pivoting on her heel and heading out of the room.

“Remember, the leisurely bike!” Shirou reminded her.

“Right, right...” Rider growled, grinding her teeth together as she left.

##

This was the most embarrassing ride she’d ever had in her life.

Despite having the Riding skill at rank A+, there was no joy to be found in this ride for the legendary Gorgon Medusa, as she couldn’t even get up to the speeds she wished to in order to let out her anger. For all her supernatural skill and talent, this pathetic mount barely had the horsepower to go above a casual speed, one that was most comfortable driving within a city street. She couldn’t even go fast enough to cut between cars and lanes!.

To Rider, it was all a reminder of how pissed off she was at the fact she was now barred from her regular means of transportation.

She had to get back at Shirou for this, one way or another. No matter how dear he was to her or even to Sakura, he had crossed a line. One that left her incapable of letting out the full scale of her stress and getting any semblance of satisfaction out of riding. Nothing about this was helping, and she had her doubts she would see combat for a time, so there was no other way she could vent out this anger she had pent up.

Then she spotted it.

Without realization, Rider had reached the edge of one of Fuyuki’s less reputable districts, one nearly devoid of color and brimming with the potential for danger of many varieties. Not that any of it was a threat to her of course. In front of her was an adult store she had only eyed a few times throughout her many wild rides by mere chance, having only ever taken it into consideration as a means to stop at and look around a little. But now she had all the reason in the world to step inside and thoroughly peruse its wares. And so she parked her bike and strode inside with a burning passion like none other that threatened to boil her blood, with a specific goal in mind.

It didn't matter to her whether Shirou would like what she had planned or not, he was going to learn the hard way not to mess with her like this.

##

“Shirou, I'm home!”

Shirou put down his book as Rider announced her return to the Emiya household, inhaling through his nostrils. He hoped the time she’d spent outside and on the leisurely bike was enough to get her to calm down, and was prepared to discuss things further with the purple haired Servant. However, when she walked in with a black plastic bag, his curiosity was piqued.

“Rider, where did you go?” he asked. “That doesn't look like a bag from the grocery store...”

“You shall see soon enough,” Rider said as she adjusted her glasses, “but I want you to meet me in my bedroom, as soon as possible.”

There was suspicion from Emiya as she said this, to be sure, but after a brief consideration he decided some sexual aggression from Medusa would be enough to get her to calm down about the bike situation. Perhaps she'd see things his way when she felt the relief wash over her after a satisfying climax.

By the time he arrived in her room, his jaw dropped. Rider was already in her combat gear, her blindfold protecting him from her mystic gaze. “Whoa...I didn't think you'd be getting into this sort of role, Rider.” Shirou said to the purple haired servant.

“You do realize that you've messed with a Rider's passion, yes?” she asked, her voice both deadly and captivating. “Undress yourself. Now.”

There were a lot of thoughts going on in Shirou's mind, two being consecutive after one another. The first was that he didn't have to go along with this. The next thought, however, was that he had a feeling Rider wasn't going to give him a choice in the matter.

Seeing no alternative, and admittedly turned on, Shirou did as she asked, stripping down to his birthday suit even as his cheeks turned bright red. “Good slave,” Rider said, approaching the nude, well-muscled young man. She closed her eyes and took off her blindfold, placing it over his face instead. For some reason, he felt inherently blinded by it, lacking in the senses that Rider had to compensate for it otherwise. “How do you feel, my handsome slave?”

“I...can't really see.” he replied awkwardly.

“That’s the idea.” Rider said, placing her glasses over her face to protect from the chance she might turn him to stone. She then grabbed Shirou by his wrists, placing them behind his back. The red haired boy groaned, struggling on instinct alone until the purple haired woman pushed her foot into his back knee. Shirou fell, allowing her to use some rope to tie his wrists behind his back.

“Don't try to struggle with this,” Rider insisted, tapping her palm against his cheek, “you're about to learn the hard way how I deal with people who suppress my riding inhibitions.” She then dragged her fingernails against the back of Shirou's neck, watching him shiver even as it was done so with a feather-light touch. Shirou seemingly had no idea how quickly the feeling of her finger could change from gentle teasing to rough scratching, and yet it seemed to be something he liked, as Rider saw with his cock slowly growing erect.

“You're enjoying that,” she laughed, “good, anything that will help stimulate your senses and let you know your place warms my heart. I seem to be getting that same sense of adrenaline by dominating you, Shirou, but this is far from the highlight of the session.”

“That's...great...” Shirou groaned as Rider continued to pet his neck, rubbing her fingernails into his skin lightly. She circled around to his chest, running down his torso until she forced him to his feet. Smiling at his vulnerability, she saw an opportunity to continue teasing him, and brought about another toy from her bag: a steel pinwheel. She was especially curious to see what would happen when used around a certain body part. “Now stand still. I'm not trying to hurt you with this.”

Her warning still startled Shirou, “Hurt me with wha-haaaaaa...” Shirou sighed and gasped near-simultaneously, his body tensing up as the spikes on the pinwheel pushed into the skin around his cock, which throbbed and bounced about as he tried to stay in place. She was getting a thrill out of seeing him shiver. It seemed the cold press of the pins were getting to him. Rider was amused, using her other hand to play with her pelvic region through the fabric of her outfit. As Shirou's precum started leaking from the urethral slit, she could see he was clearly aroused, even if he didn't want to fully admit to it.

As her adrenaline rose up, her interest in punishing Shirou did as well. This playful means of sensory deprivation was fun, but she wasn't going to be satisfied until she heard him screaming her name. And while there were quite a few ways she could accomplish that, she was craving one particular method far more than any other.

“Come this way, Shirou,” Rider insisted, pulling Shirou by his cock and leading him to the bed. The young man groaned as she gripped the shaft tightly, as if she was intent on squeezing every drop of precum out of him. He was then shoved onto the bed, bent over it with little means of moving thanks to his bound wrists.

“Rider... what's your intent here?” Shirou groaned.

“To make you squeal, of course,” Rider replied, pulling out the pride and joy of her recent purchases. She licked her lips as she stared at the ten inch dildo, black with a silicone finish, as she knew this was going to be quite the thrill for herself. It would be especially fun to see how Shirou handled it, for she was certain he had never taken anything up his ass prior. “I hope you're ready for this...” Rider said, removing her panties and pulling up the skirt portion of her outfit as she strapped the toy around her waist by means of a harness.

“Wait,” Shirou said, hearing the straps and buckles fastening and connecting the dots with his current position, “Rider, wait, don’t you d-” Shirou's spine arched, his teeth clenched together as he shut his eyes tightly behind the blindfold. Rider had swiftly shoved the head of her girth into his asshole, though it was particularly raw on his end. The silicone dildo slid slowly up his rectal cavity, stretching it out to fit inside him. But it was such a slow trip, there was no way for him to feel comfortable with the device going inside him.

Shirou wasn't helped by the fact that, as it was getting harder to fit the whole toy inside him, Rider would buck into him to make it possible. She laughed all the while, even reaching for a plastic paddle that she used to smack his rear, meanwhile her other hand kept a firm hold of his bound wrists to keep him in place. The young man groaned and gasped, even as this allowed for his anus to loosen up. This made the toy cock's trip up his ass a little easier, but not by much.

“You know, Shirou, it was fun to mount Number One and have a thrill riding at such ludicrous speeds.” Rider said with another smack of the paddle, followed by another push as her hips finally made contact with Shirou’s rear. “But until I regain the privilege to ride it, I think I'm going to have to entertain myself with a new mount.”

“And... what would... that mount be?” groaned Shirou as the purple haired woman leaned into him.

“You.” Rider whispered, proceeding to blow air into his ear canal. Shirou shivered, finding himself unusually relaxed by that sudden, tender moment. It didn't last very long, as the purple haired woman proceeded to stand upright, rearing back before she bucked away at his behind, hearing him growl as the dry silicone shaft massaged into his prostate. His cock bounced with every thrust made by Rider and her powerful hips, literally riding him throughout.

“I hope you think this is fun, Shirou,” Rider laughed before using the paddle once again, “because I'm going to enjoy riding you to orgasm over, and over, and over...”

Leaning over him again, Rider couldn't help but bring her fingers around to Shirou's mouth as her other arm wrapped around his waist, forcing him to open up so she could jut her digits inside. Inaudible glucks escaped from his lips, with the purple haired woman taking the time to slow her motions down briefly. That didn't stop her thrusts from having even more weight to them, as the redhead felt as well as heard the louder sounds from her waist meeting with his ass.

When Rider pulled her fingers out of Shirou's mouth, his saliva pooled onto his chin, dripping over the bed before landing atop the sheets. As the purple haired woman leaned back and took a firm grip of both his hips, she proceeded to slam her pelvis furiously against his ass, each one producing a meaty smack of flesh on flesh. Amidst his moaning, Shirou swallowed his own drool before it could pool out yet again, though his voice grew ever higher in pitch. The woman laughed, already aware of what that sound implied.

“Why, Shirou, don't tell me you're already close to cumming?” she teased. “What a shame, I thought you could try to ride this out just a bit longer. I suppose you don't have the same stamina you would when you're in charge. But then again, you've never been in such a kinky position before, I imagine.”

“You're... not wrong about that...” Shirou groaned, doing his best to hold back the urges that filled his mind.

He found himself flipped over by Rider, ending up not only on his back, but resting atop his wrists as well. She continued to buck into Shirou's ass, holding him up by his legs to get the best access to his rear for her toy cock to travel up his asshole.

From here, she could watch his cock and balls bounce with every motion her pelvis made against his backside, with the tip of her silicone dong looking to push deeper than it could actually get. She moved faster against him, with the toy now adjusted to his anus even as it rubbed over his prostate. Precum oozed down his shaft, which Rider was more than willing to tug on. It was nice and meaty, and in any other situation she would want to either suck on it or let him stuff it in her pussy.

However, this was a punishment for Shirou. She wanted to remind him who was boss when it came to Number One and how she used it, damages and repairs be damned.

Rider pumped the cock faster against Shirou’s ass, the sounds of skin on skin almost echoing around the room. She was adamant to get him off, and it was clear to the young man as that occurred. Nothing he could say was going to get her to stop, as she seemed to make it a mission to make him cum. He just wished he could get her to jerk him off, but for some reason she was adamant on only focusing on his rear.

The thing was though… it was working.

“That's it, Shirou,” Rider smiled, “you're getting closer, aren’t you? It must be a nice feeling when you're the one being mounted for a change. Let's see how much the master of the Emiya household likes it when he's the one taken for a ride.”

While Rider pumped as hard as she could, her eye on his shaft as it bounced with every hump against his ass. She was getting a thrill out of the sight, standing over Shirou as she watched him struggle to hold his release back any longer. There was nothing he could do though, as she was growing intense with attention to his cavity. He clenched his teeth, his head tilting back as he hit his peak. Even when seeing that he was ready to explode, she didn't stop pumping her hips into him, determined to keep thrusting until he was well over the finish line.

Before he reached his peak though, Rider removed the blindfold from his eyes, as she wanted to see the look on his face. She of course already had her glasses on at this point, so as to keep him from being turned to stone.

As he finally released his seed, Shirou arched his back, roaring loudly as the first string sprung high into the air, almost like a geyser going off. The way his eyes were strained, teeming with desperation and denial, was exactly what she wanted to see. Clearly, bbeing brought to climax solely through stimulation of the prostate was a very different experience for him. Rider cackled as his ejaculate almost met with her face, splashing back down on his torso. Every shot from his slit after that was nothing in comparison, but it was still fun to see just how much of the creamy substance he had stored up in his balls. Even with his ass still being rubbed by the toy shaft, his body quivered, hoping that she would stop soon.

Rider pulled out of Shirou when it was clear he was finished releasing his jizz, hearing him gasp and pant loudly after that. The purple haired woman was thrilled to see him in such a state, worn down heavily by the actions of the Servant.

“Okay, Rider...” Shirou sighed. “You've taught me your lesson. I won't restrict your use of Number One...”

“You think I'm finished?” Rider asked with a mischievous laugh, tying the blindfold back around his eyes. “Shirou, we're far from done here. And since I still have use for your ass, I want you to wear this until I'm ready to pound you further.”

“What is it...?” Shirou asked with a gulp.

“You'll feel it in a second.” Rider laughed to herself, adjusting her glasses as she stared at the buttplug she bought that matched with her dildo in everything but length. “It's not as big, and I suppose I should have trained you with it first. But with how thick it is I'm sure it will fit inside you just fine.”

“That worries me...” Shirou said just before she prodded it against his anus. His toes curled in as he expected the worst, even if he couldn’t see what was about to go up his ass and remain there.


	2. Chapter 2

"Now stand up, Shirou. Let's see how you walk."

The master of the Emiya household struggled to even sit upright, thanks to his wrists still being tied together behind him. Even when he did so, he could already feel discomfort creeping into his rectum. The buttplug wasn’t even half as long as Rider's toy cock, but it still left a strain on his anal cavity. He groaned as he managed to scoot off the bed, his feet touching the floor as he finally managed to stand before the purple haired woman.

"Come on," Rider said, teasing Shirou further by giving the plug's base a wiggle, "take a few steps and show me how comfy you are having that thing inside you."

Doing the best he could, Shirou took tiny steps forward, even then feeling the toy wriggle about in his ass. With how small and shakily he walked, Rider couldn't help but laugh at him, amused that he could only move at such a sluggish speed. Getting the paddle in her hand once again, the purple haired woman was quick to bring it to his cheek, causing it to swell up from the repeated spankings he had been given throughout the session.

"Come on, walk like you mean it!" Rider yelled out. "Think about it like you're on a stroll. Or would you rather I have you walk from here to the bathroom where everyone else might see you walking so shamelessly?"

Grumbling, Shirou did as the Rider asked him to, though there was concern on his end; he was still wearing her blindfold, meaning it was hard for him to see where he was going. Blinded by a visual only she could recognize, the head of the household had to be careful, or else he could risk walking into a leg intended to trip him up.

While he put his trust into Rider, he never would have imagined how malicious she could be when it came to her need for speed.

He paced around the room, the plug still snug inside his anus. He had slowly grown comfortable with the device forced inside him, though it was still awkward to walk. The toy brought a slight limp into his step, making him question if it would stick with him at the worst times. He didn’t even want to think about what this thing would do to him if he were to wear it in a battle.

"Excellent job, Shirou," Rider said in a condescending tone, "now let's see what happens when you're being tickled from the inside."

"Wait, what?!" When the plug began to vibrate, Shirou brought his legs together, squeezing them tightly. It was too much for him to handle, especially with the friction coming from the inside of his ass. It was nothing too comfortable on his end, though the fact it was rubbing against his prostate caused him to quiver.

Still entertained by the punishment of the young man, Rider watched his cock spring back to life, even as there was still some seed leaking from the slit. It bounced about as it rose to its full erection, likely thanks to the vibrating functions of the butt plug.

"You walk in such a cute manner, Shirou!" Rider said, teasing the back of his neck to watch him shiver. "And all thanks to that butt plug." She turned the device off for the time, only because as much as she would love to see it, she didn't want to overstimulate him, either.

"C-Can you pull it out now, please...?" Shirou asked, heaving as he kept his legs close once again.

"Only when I feel like putting my cock back in you." Rider said, pinching Shirou's cheek. "There's still so much I want to do to toy with you, too!"

"Like...what...?" Shirou sighed, as he yet again found Rider slowly brushing her nails against his neck, as if he we're a feline looking to be petted. However, her nails were a bit colder, and just a hint sharper. It was like steel on his skin, which was exactly what she was using.

As he leaned his head to the side, Rider laughed. "Do you like it?" she asked. "I think you've shown enough enjoyment to at least try them out."

"They're...fine..." Shirou said with a heavy exhale. It was a different feeling compared to just her nails, but it was clear he was getting some sort of thrill. His body adjusted to the kinky stimulation she was bringing to him, especially when she leaned into his ear again. This time she nibbled down lightly on his ear, hearing him breathe louder. It was apparent he was sensitive in that location, and the closeness between them brought Rider to want to toy with him more.

She had bought so many toys, in fact, she didn't even know if she would get to use them all before her ride became exhausted.

"How is your ass feeling, Shirou?" Rider whispered. “Is your asshole hungering for my cock once again?"

"Yes..." Shirou confessed in a moment of weakness.

"Splendid, but before we get to that, let's see if we can lube it up a little with your mouth first. It seems like that would make it easier for me to slide around when I’m pounding your ass."

Pivoting around the young man, Rider stood before Shirou with her cock poking against his tip. As she found more precum oozing at the slit, she swung the toy back and forth against it just to get it on her tip. Even if it did little to help, it was just a fun thing for her to do and taunt the head of the house even further.

Shirou was brought to his knees, with Rider holding his scalp in place before she pushed her hips into him. His mouth was soon filled with her toy cock, which he kept open even as it pushed all the way to the back. The silicone shaft managed to push into his throat, causing the head of the house to hack and gag on the thickness that it brought. He strained to breathe properly, even as his throat was stretched out by the fake member.

As the harness straddled against her waist, Rider moaned with pleasure as she finally felt a sense of stimulation to her private parts. With the garments of her battle outfit gone, she could feel her fluids dripping from the folds and landing on the fabric. As she bucked into his face, Shirou's saliva continued to leak from his mouth, dripping down his chin. The balls molded into the dildo smacked into his lower lip, with his drool moistening them on impact with his face.

“Your mouth is filled with saliva, Shirou,” Rider groaned as she held his lips to her waist, “it would be such a waste if we didn't use it all. Go ahead and cover my cock with your spit!” Shirou did as he was told, gathering all of it onto the dong before trying to pull back from the cock's base. The purple haired woman finally let go of his hair, watching him gasp for air while grabbing at his throat.

“How can you do that so casually...?” Shirou asked, his first experience with deep-throating having proven a difficult one. He thought about their previous sexual exchanges, wondering how she could handle his own member when she was the one performing oral. While he obviously wasn’t as large as Rider’s dildo, he was big enough that the head of his cock was quite familiar with how her throat felt. Though, he wasn’t sure how often he’d be feeling that sensation again in the future...

“A lot of practice,” Rider confessed, helping Shirou back to his feet. “Which you’ll certainly be getting in the future, my mount. Right now though, you have an ass that needs fucking.” She then reached for the butt plug and swiftly pulled it out with a pop, while at the same time bringing her nails down over his member to tease him even further. She was especially playful with the crown, teasing her fingernail against the slit, looking up at the young man as his teeth were clenched tightly. With how she had been doing almost everything to him throughout the day, he seemed to expect something to go up there. She merely left the nail at the edge, though wouldn't go any further. Even she knew he was never going to be ready for that.

But with the dildo smothered in spit, Rider bent Shirou over, pressing her palm down on his wrists as she kept him in place. She poked against his now-dilated asshole once more, ready to slip inside with ease. It didn't go as smoothly as she wanted, as Shirou inhaled oxygen loudly as she inserted her toy into him. It was music to her ears nonetheless, and this time it had only taken a single long push for Rider to get her whole cock all the way up Shirou’s rectum. There was definitely less resistance compared to before, with his anal cavity already growing accustumed to her toy member.

Rider kept her fingers on the pulse, almost literally, as she felt against Shirou’s crown to feel his heartbeat racing. She reared back for more hard bucking, with the balls on her toy smacking hard into Shirou's taint. The young man gasped with every slap against his ass, the harness of the purple haired woman impacting him hard.

“Oh, there's still so much for me to use...” Rider sighed, tapping her finger against her lips. “Here, Shirou, let me lead you back to the bed.”

To Shirou's surprise, Rider grabbed his legs and lifted him off his feet, making him feel as if he was on display for an audience that wasn't present. His cock bounced with every step the woman took, while his sphincter clenched down on the toy rod. A trail of precum led from where they were back to the bed, with the Rider proceeding to grab another item from her bag; a leather crop.

With Shirou brought back to his feet, Rider had him standing upright before the bed as she rubbed her latest toy against the length of his shaft and she once again began to repeatedly thrust her toy in and out of his asshole. She licked her lips as she pressed the crop against the tip of his dick, pulling back to see just how sticky the precum was. It didn't get very far before the strand of liquid broke between the two, but it was fun for her to at least try out. She then massaged it over the length of his cock before slapping it down on the crown, prompting Shirou to tense up even further and let out another stifled groan.

“Don't tell me that was too much for you,” laughed Rider as she ran her finger under his chin and put just a little bit more power into the swing of her hips, “after all I've put you through?”

Shirou said nothing, with his train of thought having evolved along this crazy ride the woman had taken him on. At first, he was in disbelief that any of this was happening in the first place, but as she continued to use and abuse him, making him her mount for a long period of their time together, he couldn't help but think how wrong it was, and yet how it felt so good.

If this kept up, who knew where his mind would wander...

Rider paused in her frequent thrusts into Shirou's ass, purring as she watched him turn his head in confusion. Even as he wore her blindfold, she could see him responding to her abrupt end to reaming his ass, though she still kept her cock balls deep inside him.

“You want me to keep fucking your ass, don't you, Shirou?”

“N-Not in the slightest!” Shirou replied, turning his head to face forward and keep the Servant from seeing his cheeks light up. “I just thought you’d want to keep going.”

“Do you want me to?” Rider asked, slapping the crop down on his cock repeatedly.

“Well, you're the one riding me...” Shirou groaned, squirting some precum which flew surprisingly far.

“That doesn't answer the question.” Rider brought the crop down to Shirou's ball sack, massaging the leather tip against the skin. Pleasure came to her ears as he whimpered, worried about her consideration to smack his nuts with her toy. “Do you want me to keep going?”

“Yes! Yes, please!” Shirou begged, his eyes closed under the blindfold as he went through with the confession. “I love how you fuck my ass, please keep going!”

“Keep going...what?” Rider asked, rearing the crop back.

“Mistress! Keep going, mistress!”

She lowered the crop, almost disappointed that he’d so quickly found the magic word. “Very well then, my mount. You should probably prepare yourself, however. I always get a thrill out of riding you faster.”

Holding the head of the house by his waist, Rider pulls back on Shirou, keeping him close as she sits down on the bed. The young man shivered, his toes curling in as sitting atop her lap caused a deeper push inside his rectal cavity. Like before, this new position with the purple haired servant made him feel as though he were on display, even though there was nobody else in the room with them.

That thought did cross his mind, however; what if there was someone else with them hiding in the closet? Could Sakura have wanted to witness his sexual humiliation and embarrassment, or any of the other ladies under his household? Even if he didn't know the reasoning behind it, the thought somehow aroused him even more, which he never even thought to be possible at this rate.

“Come on, Shirou,” Rider said, tapping the crop on his crown again, “I want you to move about now.”

“W-what? What do you mean?” She tapped his dick with the crop again. “Mistress.”

“You're still the one riding my cock,” she reminded him. “But now you're in control. So start riding it like a good little mount.”

Shirou sighed, rocking his hips back and forth on her shaft to stimulate his prostate, biting down on his lower lip as he did so. There was little else he could do to move about, as his wrists were still tied up behind his back. Rider was at least enjoying the view, seeing his behind squish down on her lap as he rocked about. It was nice to have him do some of the work for a change, especially as she knew she was going to have to let go her rush of adrenaline at some point.

The Servant could at least see that Shirou was enjoying his position the longer he rode atop her, finally squatting atop the toy rod with some impact in his drops. The impact of skin on skin was loud, echoing within the room along with the young man's grunts. He was sounding more and more like the women in those porn videos Rider had found, even if his pitch didn't match up with that of the actresses.

As Shirou bounced on top of her, his balls dropped down on the ones molded into her toy cock. It wasn't painful for him, in fact it was aiding in a need he’d been receiving from Rider throughout this second rise in an erection. She had done many things to his cock, slapping it, teasing it, massaging it, but compared to before, he noticed that as the veins pumped hard on his member, Rider wasn't bothering to properly tug on his shaft. He was growing desperate for a release, and had hoped she would assist in that without needing to say anything. He did his best not to pester on it, concerned he might just end up with more punishment from her, especially towards his sack.

“Come on, you're so close,” Rider said, “I can tell. You're going to have to release that load sooner or later.”

Curious, Shirou tried something, as uncomfortable as it was. He managed to lift his legs onto the bed, circling around while the cock was still up his ass. It was something Rider hadn't anticipated him to do, and yet she could see why; not only was it a call to attention, begging her to help him get off, but also so he could shoot his cream into her face when the time finally arrived. She laughed at the idea, as it didn't even bother her in the slightest. She was anticipating the eventual release, knowing he wouldn't have any energy following it.

Desperate for that climax, Shirou squatted faster and harder, his balls dropping down atop Rider's lap. Even with the blindfold on, she could see that he was going crazy without that release. He was trying to look at her with begging eyes, wanting assistance in some manner. And yet, the Servant refused, as she wanted to prove a point in regards to what was happening.

“Ri-...Mistress,” Shirou said, quickly correcting himself, “I need to cum! Please, help me...cum! Please fuck me!”

Cackling, Rider slapped her palm against Shirou’s ass, seeing how desperate he had become. “Silly boy! You can’t even drain your oil without my help? Then allow me to assist you!”

Hoisting up his thighs, the Servant was ready to give him an aggressive pounding. Even as she laid on her back, Rider was able to thrust upwards against Shirou’s ass, watching him tremble atop her. The shaft repeatedly massaged over his prostate, with the repeated bumping causing his dick to throb. Seeing him having to rely on her assistance was perhaps the greatest pleasure she could receive from her interactions with the young man, showing that he was far too dependent on her. That’s how she wanted it; Shirou was her ride, and nobody could get him going except her.

Finally, Shirou's body gave out, finding himself slouching atop Rider as the toy pressed over his prostate one last time. The young man quivered and let his seed loose. The strings of cum shot out so high it hit Shirou’s own face, a sight that delighted Rider. Everything following that was mostly below the neck, landing on his chest and torso.

Shirou's mouth gaped widely as he finished, still shaking from the way he managed the climax. It was an incredible feeling, as that orgasm was the most intense he’d ever had.

Finished, Rider released his legs and Shirou tried his best to roll off of her, a feat he managed as she let her cock pop out of his anus. He laid next to her, letting the Servant cuddle up with him afterwards. “So, how did that feel, Shirou?” she asked, removing the blindfold and letting Shirou look her in the eye.

“Good...very...very good.” Shirou replied as he caught his breath. “I can’t believe I came like that...”

Rider chuckled, running her fingers over his chest. “And I imagine you’re pondering how you only came after I helped you. Correct, my mount?”

“It was weird, but… yes.” Shirou admitted.

“It's very simple. The first time was to make you realize you didn't cum because of pleasure brought to your cock; you came because you pleased your prostate against my cock.”

As she removed the blindfold from his eyes, she could see his irises shrinking as he had a moment of panic. “That, that's just-”

“And this time,” Rider interrupted him, “Even when you had control over the toy up your ass, it still wasn’t enough. You needed me, your mistress, to fuck your ass in order to cum. There’s a simple explanation for this, Shirou: You love having your ass fucked by my cock. You love being a submissive bitch, to me especially. And you love being my mount. You may still be in denial over these facts, but it's all the simple truth. You just never had any way of knowing it until now.”

“N-No, that… that can't be true...” Shirou begged.

“It's fine,” Rider said, stroking his face with a mixture of affection and possessiveness. “You may not understand it right away, at least not on a conscious level, but that's quite all right. I'm more than happy to teach you, Shirou, and help you accept your role in the bedroom.”

The purple haired Servant purred, nibbling on Shirou's ear, and once again placing the butt plug inside him. The young man moaned, curling his toes in from the sensation it brought. It was such a tease, as he knew she wasn't going to bring him to climax again so soon after that explosive revelation.

Truly, he had a lot to think about before he went to bed.

**Author's Note:**

> Thank you for reading! Chapter two will be released publicly in a few days.
> 
> If you'd like to follow for more content and community, as well as updates on my content, be sure to visit me here:  
> https://discord.gg/UEYU52  
> And here: https://twitter.com/HeroicFizzer


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